While transgenderism as a cultural phenomenon seems to be based on a collective taste for the sensational, its emergence represents a collective shift towards a new or more differentiated way of experiencing and expressing sex and gender, a movement of world soul. This paper attempts to explore that emergence from a Jungian perspective. The paper utilizes clinical examples which illustrate how dissociated aspects of the personality are seeking assimilation and expression in order to move the personality towards greater wholeness. In that sense, it attempts to understand the teleology of transgenderism on an individual and collective level. The paper is intended as a starting-off point for discussion and explores gender as fantasy, anima/animus dynamics, the psyche/soma relationship, the role of hormones/biochemistry in our experience of ourselves and what transgender people carry and suffer for our culture.